CN115636857B - Compound, composition, extract and application thereof in preparation of products with relieving effect - Google Patents
Compound, composition, extract and application thereof in preparation of products with relieving effect Download PDFInfo
- Publication number
- CN115636857B CN115636857B CN202211340546.2A CN202211340546A CN115636857B CN 115636857 B CN115636857 B CN 115636857B CN 202211340546 A CN202211340546 A CN 202211340546A CN 115636857 B CN115636857 B CN 115636857B
- Authority
- CN
- China
- Prior art keywords
- sang
- extract
- glycoside
- formula
- bushuang
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 230000000694 effects Effects 0.000 title claims abstract description 39
- 150000001875 compounds Chemical class 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 13
- 239000000284 extract Substances 0.000 title abstract description 56
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 13
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 12
- 239000002537 cosmetic Substances 0.000 claims abstract description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 229930182470 glycoside Natural products 0.000 abstract description 53
- 150000002338 glycosides Chemical class 0.000 abstract description 39
- -1 disaccharide glycoside Chemical class 0.000 abstract description 22
- 239000003814 drug Substances 0.000 abstract description 16
- 229940079593 drug Drugs 0.000 abstract description 12
- 240000004385 Centaurea cyanus Species 0.000 abstract description 6
- 235000005940 Centaurea cyanus Nutrition 0.000 abstract description 6
- 230000003064 anti-oxidating effect Effects 0.000 abstract description 5
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 238000011160 research Methods 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 45
- 235000010208 anthocyanin Nutrition 0.000 description 44
- 229930002877 anthocyanin Natural products 0.000 description 44
- 239000004410 anthocyanin Substances 0.000 description 44
- 150000004636 anthocyanins Chemical class 0.000 description 41
- 238000004440 column chromatography Methods 0.000 description 21
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 15
- 239000012528 membrane Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 239000013641 positive control Substances 0.000 description 14
- 229930182478 glucoside Natural products 0.000 description 13
- 240000004153 Hibiscus sabdariffa Species 0.000 description 12
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 12
- 150000008131 glucosides Chemical group 0.000 description 12
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000004952 Polyamide Substances 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000012535 impurity Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 238000010298 pulverizing process Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001728 nano-filtration Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002791 soaking Methods 0.000 description 6
- BIVBRWYINDPWKA-VLQRKCJKSA-L Glycyrrhizinate dipotassium Chemical compound [K+].[K+].O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H]1CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@](C)(CC[C@@]5(CC[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C)C)C(O)=O)C([O-])=O)[C@@H]1O[C@H](C([O-])=O)[C@@H](O)[C@H](O)[C@H]1O BIVBRWYINDPWKA-VLQRKCJKSA-L 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 229940101029 dipotassium glycyrrhizinate Drugs 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 238000001471 micro-filtration Methods 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- 238000011161 development Methods 0.000 description 4
- 210000002257 embryonic structure Anatomy 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000000108 ultra-filtration Methods 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 3
- 241000252212 Danio rerio Species 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 150000002016 disaccharides Chemical class 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 241001164374 Calyx Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000202296 Delphinium Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 1
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 1
- 241000219071 Malvaceae Species 0.000 description 1
- 244000038561 Modiola caroliniana Species 0.000 description 1
- 235000010703 Modiola caroliniana Nutrition 0.000 description 1
- 244000078534 Vaccinium myrtillus Species 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000002792 antioxidant assay Methods 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical class O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a compound, a composition, an extract and application thereof in preparing a product with a relieving effect. The compound has a structure shown in a formula I or a formula II. The composition comprises a compound with a structure shown as a formula I and a formula II. The extract contains compounds with structures shown in formula I and formula II. Research shows that cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bu disaccharide glycoside have soothing activity; and also has anti-inflammatory and antioxidant activities. Therefore, the cornflower extract-3-Sang Bushuang glycoside or delphinidin-3-Sang Bushuang glycoside, a composition of the two, or an extract containing the cornflower extract-3-Sang Bushuang glycoside and/or the delphinidin-3-Sang Bushuang glycoside is used as an active ingredient, and has important application value in preparing cosmetics, skin care products or medicines with relieving effect, especially in preparing cosmetics, skin care products or medicines with relieving, anti-inflammatory and anti-oxidation effects.
Description
Technical Field
The invention relates to the technical field of natural products, in particular to a compound, a composition, an extract and application thereof in preparing a product with a relieving effect.
Background
Anthocyanin belongs to flavonoid compounds, has a basic skeleton of C3-C6-C3, and belongs to derivatives of 2-phenyl chromone. The parent of anthocyanin is anthocyanin, and stability is poor, so that anthocyanin exists in the natural world in a glucoside form of anthocyanin combined with different sugars, namely anthocyanin. Anthocyanin widely exists in flowers, fruits, stems and leaves of various plants and is a water-soluble pigment. Pharmacological studies show that anthocyanin has various effects of anti-inflammatory, antioxidant, anti-tumor and the like, and cardiovascular disease and the like, and has wide application in health food [ the research current situation and the hope of biological activity of anthocyanin compounds, food industry science and technology, 2017, 38 (16), 335-340]. In Europe, the anthocyanin content in the pigment extract is more than 24%, and the pigment extract can be used as a medicine, wherein the Vaccinium myrtillus anthocyanin is recorded in Germany pharmacopoeia [ current research situation and development trend of anthocyanin extraction and purification, chinese food additive, 2008, 147-150]. In the 21 st century, the health industry has grown and rapidly grown, and anthocyanin has been attracting more and more attention as an excellent free radical scavenger. However, whether anthocyanin has a relieving effect or not is reported in the prior art.
Roselle is a calyx part of roselle, a malvaceae plant, and is rich in anthocyanin components. Therefore, the compound, the composition or the extract with the soothing effect is developed by taking the roselle as the raw material, and has important application value. In particular to the development of a compound, a composition or an extract with the effects of relieving, resisting inflammation and resisting oxidation, which has more important application value.
Disclosure of Invention
In order to overcome at least one of the technical problems in the prior art, the present invention firstly provides a compound, a composition and an extract.
The technical problems to be solved by the invention are realized by the following technical scheme:
the invention firstly provides a compound, which has a structure shown as a formula I or a formula II:
The compound with the structure shown in the formula I is cyanidin-3-Sang Bushuang glucoside; the CAS number is: 63535-17-1.
The compound with the structure shown in the formula II is delphinidin-3-Sang Bushuang glucoside; the CAS number is: 178275-92-8.
The inventors have surprisingly found in the study that both of the above-mentioned cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bu disaccharide glycoside have soothing activity; it can be used as active ingredient for preparing cosmetic, skin care product or medicine with relieving effect.
Further studies by the inventors have also found that both cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bu disaccharide glycoside also have anti-inflammatory and antioxidant activity; therefore, the cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bu disaccharide glycoside can be used as active ingredients for preparing cosmetics, skin care products or medicines with the effects of relieving, anti-inflammatory and anti-oxidation.
The invention also provides a composition which comprises the compounds with the structures shown in the formulas I and II.
The inventors have surprisingly found in further studies that, after the cornflower-3-Sang Bushuang glycoside and delphinidin-3-Sang Bu disaccharide glycoside of the structures shown in the formula I and the formula II are combined, the cornflower-3-Sang Bushuang glycoside and the delphinidin-3-Sang Bu disaccharide glycoside have a synergistic relieving effect and also have a synergistic antioxidation effect; the combination of the cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bu disaccharide glycoside with the structures shown in the formulas I and II has very excellent relieving and antioxidant effects, and the relieving and antioxidant effects are obviously higher than that of the cyanidin-3-Sang Bushuang glycoside or the delphinidin-3-Sang Bushuang glycoside alone. The relieving effect is higher than that of the positive control medicine dipotassium glycyrrhizinate; the antioxidation effect is higher than that of the positive control medicine tert-butyl hydroperoxide glutathione.
Preferably, the weight ratio of the compounds of the structures shown in the formulas I and II is 1-5:1-5.
Further preferably, the weight ratio of the compounds of the structures of formula I and formula II is 1-3:1-3.
Most preferably, the weight ratio of the compounds of the structures of formula I and formula II is 2-3:1.
The invention also provides an extract which comprises the compounds with the structures shown in the formulas I and II; the total weight percentage of the compounds with the structures shown in the formulas I and II accounts for more than 30% of the weight of the extract.
The cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bu disaccharide glycoside with the structures shown in the formulas I and II have the effects of relieving, resisting inflammation and resisting oxidation. Thus, it was determined that extracts containing the cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bushuang glycoside of the structures shown in formulas I and II also have soothing effects, as well as anti-inflammatory and antioxidant effects.
Preferably, the total weight percentage of the compounds of the structures represented by formula I and formula II is more than 60% of the weight of the extract.
Preferably, the total weight percentage of the compounds of the structures represented by formula I and formula II is more than 80% of the weight of the extract.
The invention also provides a preparation method of the extract, which takes roselle as a raw material, and the extract is prepared by extracting with water, filtering, and carrying out macroporous resin column chromatography and/or polyamide column chromatography.
Compared with the existing method for preparing anthocyanin compounds, the method provided by the invention has the advantages that only low-concentration ethanol is used as the organic solvent, and the other organic solvents are all water-phase operation, so that the preparation cost is low, and the process is simple and environment-friendly.
Preferably, the preparation method specifically comprises the following steps:
(1) Pulverizing Hibiscus sabdariffa, and extracting with water to obtain extractive solution;
(2) Ultrafiltering the extracting solution with ultrafilter film of 8-12 KD to obtain dilute anthocyanin solution;
(3) Nanofiltration is carried out on the anthocyanin dilute solution with a nanofiltration membrane of 100-200D, and the filtrate is concentrated to obtain anthocyanin concentrated solution;
(4) And (3) subjecting the anthocyanin concentrate to macroporous resin D101 column chromatography, eluting with 18-25% ethanol water solution, collecting eluent eluted from the 18-25% ethanol water solution, concentrating and drying to obtain the extract.
Further preferably, the preparation method further comprises a step (5); the step (5) comprises the following steps:
collecting concentrated anthocyanin refined concentrated solution obtained by eluting ethanol water solution with the volume fraction of 18-25%; subjecting the anthocyanin refined concentrated solution to polyamide column chromatography, eluting with 18-25% ethanol water solution, collecting eluate eluted from 18-25% ethanol water solution, concentrating, and drying to obtain the extract.
A great number of experimental researches by the inventor show that the extract prepared by using roselle as a raw material through water extraction, filtration and macroporous resin column chromatography and polyamide column chromatography under the conditions of the invention contains a great amount of cyanidin-3-Sang Bushuang glucoside and delphinidin-3-Sang Bushuang glucoside with structures shown in the formulas I and II; wherein the weight percentage of the cyanidin-3-Sang Bushuang glucoside and the delphinidin-3-Sang Bushuang glucoside is more than 80 percent.
The inventors herein have emphasized that, if it is desired to achieve a cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bushuang glycoside content of 80% or more; the elution conditions in macroporous resin column chromatography and polyamide column chromatography are critical; meanwhile, the use sequence of macroporous resin column chromatography and polyamide column chromatography is also very critical; the content of cyanidin-3-Sang Bushuang glucoside and delphinidin-3-Sang Bu disaccharide in the extract prepared under the elution conditions in the macroporous resin column chromatography and the polyamide column chromatography can reach more than 80 percent; meanwhile, the content of the procyanidin-3-Sang Bushuang glucoside and the delphinidin-3-Sang Bu disaccharide can reach more than 80 percent only by adopting macroporous resin column chromatography to prepare the extract by adopting polyamide column chromatography.
The invention also provides application of the compound, the composition or the extract in preparing a product with a relieving effect.
The invention also provides application of the compound, the composition or the extract in preparing a product with the effects of relieving, resisting inflammation and resisting oxidization.
Preferably, the product is a cosmetic, skin care product or pharmaceutical product.
The beneficial effects are that: the invention discovers that the cyanidin-3-Sang Bushuang glycoside with the structures shown in the formulas I and II has the soothing activity; and also has anti-inflammatory and antioxidant activities. The inventors have surprisingly found in further studies that the combination of the procyanidin-3-Sang Bushuang glycoside of the structure of formula I and formula II and delphinidin-3-Sang Bu disaccharide has a synergistic soothing effect and a synergistic antioxidant effect. Since the cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bu disaccharide glycoside with the structures shown in the formulas I and II have the relieving activity, and simultaneously have the anti-inflammatory and antioxidant activities; therefore, the cornflower extract-3-Sang Bushuang glycoside or delphinidin-3-Sang Bushuang glycoside with the structures shown in the formulas I and II, a composition of the cornflower extract-3-Sang Bushuang glycoside or the delphinidin-3-Sang Bushuang glycoside, or an extract containing the cornflower extract-3-Sang Bushuang glycoside and/or the delphinidin-3-Sang Bushuang glycoside is used as an active ingredient, and has important application value in preparing cosmetics, skin care products or medicines with relieving, anti-inflammatory and anti-oxidation effects.
Drawings
FIG. 1 is an HPLC-UV diagram of the extract prepared in example 1.
FIG. 2 is a graph showing the results of the anti-inflammatory activity test of the present invention.
FIG. 3 is a graph showing the results of the antioxidant activity test of the present invention.
Detailed Description
The present invention is further explained below with reference to specific examples, which are not intended to limit the present invention in any way.
Example 1 preparation of extract
(1) Pulverizing Hibiscus sabdariffa into coarse powder, soaking in 5 times of pure water overnight, ultrasonic extracting for three times each for 30min (40deg.C, 100% power), filtering to remove residue, and mixing extractive solutions;
(2) Removing impurities such as microorganisms by passing the extract through a 0.45 mu M microfiltration membrane; then passing through a 10KD ultrafiltration membrane with the pressure of 0.5MPa and the operating temperature of 25 ℃; obtaining anthocyanin dilute solution, then passing through a 150D nanofiltration membrane under the pressure of 1.0MPa, removing impurities such as salt and the like, and concentrating to a certain volume to obtain purple anthocyanin concentrated solution;
(3) Loading anthocyanin concentrate by wet method, performing macroporous resin D101 column chromatography, eluting with 20% ethanol water solution, collecting eluate eluted from 20% ethanol water solution, and concentrating under reduced pressure to obtain anthocyanin refined concentrate;
(4) And (3) loading anthocyanin refined concentrated solution by a wet method, performing polyamide column chromatography, eluting with an ethanol water solution with the volume fraction of 20%, collecting eluent eluted from the ethanol water solution with the volume fraction of 20%, concentrating and drying to obtain the extract.
Example 2 preparation of extract
(1) Pulverizing Hibiscus sabdariffa into coarse powder, soaking in 5 times of pure water overnight, ultrasonic extracting for three times each for 30min (40deg.C, 100% power), filtering to remove residue, and mixing extractive solutions;
(2) Removing impurities such as microorganisms by passing the extract through a 0.45 mu M microfiltration membrane; then passing through a 10KD ultrafiltration membrane with the pressure of 0.5MPa and the operating temperature of 25 ℃; obtaining anthocyanin dilute solution, then passing through a 150D nanofiltration membrane under the pressure of 1.0MPa, removing impurities such as salt and the like, and concentrating to a certain volume to obtain purple anthocyanin concentrated solution;
(3) Loading anthocyanin concentrate by wet method, performing macroporous resin D101 column chromatography, eluting with 20% ethanol water solution, collecting eluate eluted from 20% ethanol water solution, concentrating, and drying to obtain the extract.
Example 3 preparation of extract
(1) Pulverizing Hibiscus sabdariffa into coarse powder, soaking in 5 times of pure water overnight, ultrasonic extracting for three times each for 30min (40deg.C, 100% power), filtering to remove residue, and mixing extractive solutions;
(2) Removing impurities such as microorganisms by passing the extract through a 0.45 mu M microfiltration membrane; then passing through a 10KD ultrafiltration membrane with the pressure of 0.5MPa and the operating temperature of 25 ℃; obtaining anthocyanin dilute solution, then passing through a 150D nanofiltration membrane under the pressure of 1.0MPa, removing impurities such as salt and the like, and concentrating to a certain volume to obtain purple anthocyanin concentrated solution;
(3) Loading anthocyanin concentrate by wet method, performing polyamide column chromatography, eluting with 20% ethanol water solution, collecting eluate from 20% ethanol water solution, concentrating, and drying to obtain extract.
Comparative example 1 preparation of extract
Pulverizing Hibiscus sabdariffa into coarse powder, soaking in 5 times of pure water overnight, ultrasonic extracting for three times each for 30min (40deg.C, 100% power), filtering to remove residue, and mixing extractive solutions. Removing impurities such as microorganisms by passing the extract through a 0.45 mu M microfiltration membrane; concentrating and drying to obtain the extract.
Comparative example 2.
Pulverizing Hibiscus sabdariffa into coarse powder, soaking in 5 times of pure water overnight, ultrasonic extracting for three times each for 30min (40deg.C, 100% power), filtering to remove residue, mixing extractive solutions, and concentrating to obtain mauve anthocyanin concentrate. Loading anthocyanin concentrate by wet method, performing macroporous resin D101 column chromatography, eluting with 20% ethanol water solution, collecting eluate eluted with 15% ethanol water solution, concentrating, and drying to obtain the extract.
Comparative example 3
Pulverizing Hibiscus sabdariffa into coarse powder, soaking in 5 times of pure water overnight, ultrasonic extracting for three times each for 30min (40deg.C, 100% power), filtering to remove residue, and mixing extractive solutions. The extract is filtered through a 0.45 mu M microfiltration membrane to remove impurities such as microorganisms. Passing through 10KD ultrafiltration membrane with pressure of 0.5MPa and operation temperature of 25deg.C; obtaining anthocyanin dilute solution, passing through 150D nanofiltration membrane under the pressure of 1.0MPa, removing impurities such as salt, concentrating and drying the filtrate to obtain the extract.
The delphinium-3-Sang Bushuang glycoside and the cornflower-3-Sang Bu disaccharide glycoside are subjected to sesquidilution to prepare a series of concentrations of 8mg/ml,4mg/ml,2mg/ml,1mg/ml,0.5mg/ml,0.25mg/ml and 0.125mg/ml, and the detection wavelength is 520nm through HPLC-DAD analysis, the peak area is calculated, and a standard curve is drawn. The same chromatographic conditions of anthocyanin disaccharides in the obtained samples 1-5 were analyzed, and the total content of two anthocyanin types of delphinidin-3-Sang Bushuang glycoside and cornflower-3-Sang Bu disaccharide glycoside was calculated, and the results are shown in Table 1.
TABLE 1 anthocyanin content comparison in different extraction methods
| Total content of two anthocyanin | |
| The extract obtained by the method of example 1 | 80.0％ |
| The extract obtained by the method of example 2 | 32.5％ |
| Example 3 extracts obtained by the method | 44.1％ |
| Comparative example 1 extract prepared by the method | 0.6％ |
| Comparative example 2 extract prepared by the method | 16.4％ |
| Comparative example 3 extract prepared by the method | 2.2％ |
The content shows that the total content of two anthocyanin of delphinium-3-Sang Bushuang glucoside and cornflower-3-Sang Bu disaccharide glucoside can reach more than 30 percent; especially under the elution condition of the invention, macroporous resin column chromatography is adopted first, and then polyamide column chromatography is adopted to prepare the extract, wherein the total content of two anthocyanin, namely delphinium 3-Sang Bushuang glucoside and cornflower 3-Sang Bu disaccharide glucoside, can reach 80 percent.
Example 4 preparation of the composition
Taking cyanidin-3-Sang Bushuang glucoside and delphinidin-3-Sang Bu bisglucoside, and uniformly mixing according to a weight ratio of 2:1 to obtain the composition.
EXAMPLE 5 soothing Activity experiment
And selecting embryos with consistent morphology, no death and good development condition. Setting a blank group, a model group, an experimental group, a positive control group and five 24hpf embryos after screening are added to each hole of a 96-well plate, and three compound holes are formed in each group. After removing the buffer solution from each well, 200. Mu.l of holt-buffer solution was added to each well of the blank group and the model group, 200. Mu.l of 7ug/ml of the test sample drug solution was added to the test group, 200. Mu.l of 2mM dipotassium glycyrrhizinate solution was added to the positive control group, and the mixture was incubated in an incubator at 28.5℃for 1 hour. The solution was removed from each well, a blank control was added with 200. Mu.l of holt-buffer solution, a model was added with 200. Mu.l of 500. Mu.M SDS solution, an experimental set was added with 200. Mu.l of 500. Mu.M DS solution containing 7ug/ml of the test sample drug, a positive control was added with 200. Mu.l of 500. Mu.M SDS solution containing 2mM dipotassium glycyrrhizinate, and after 15min of reaction, video recording was performed for 30s per well. The second well dosing treatment and the previous photographing time interval of 30s. Recording the inversion times of embryos in each hole, calculating the average value of each group, and indicating that the fewer the inversion times of the embryos are, the stronger the relieving effect is; the experimental results are shown in Table 2.
The drugs of the experimental samples are as follows: delphinium-3-Sang Bushuang glycoside, cornflower-3-Sang Bushuang glycoside, the extracts prepared in examples 1-3, and the composition prepared in example 4;
TABLE 2 results of the soothing Activity experiments
| Number of inversions of embryo | |
| Blank group | 1 |
| Model group | 8 |
| Positive control group | 4 |
| Delphinium-3-Sang Bu bisglycoside group | 5 |
| Cornflower-3-Sang Bu bisglycosidic group | 5 |
| Example 1 extract set | 4 |
| Example 2 extract set | 6 |
| Example 3 extract set | 6 |
| Example 4 composition set | 2 |
As can be seen from the data of the anti-soothing activity test results in Table 2, the delphinium-3-Sang Bushuang glycoside, the cornflower-3-Sang Bushuang glycoside and the extract containing the delphinium-3-Sang Bushuang glycoside and the cornflower-3-Sang Bushuang glycoside of the invention all show certain soothing activity; in particular, the extract of delphinium-3-Sang Bushuang glycoside and cornflower-3-Sang Bu disaccharide glycoside which are prepared in example 1, the content of which is more than 80%, has very excellent soothing activity, and the soothing activity is equivalent to that of the positive control drug dipotassium glycyrrhizinate, and is obviously higher than that of the extracts prepared in examples 2 and 3.
As can be seen from the data of the anti-soothing activity test in table 2, the soothing effect of the composition of example 4 is significantly stronger than that of delphinium-3-Sang Bushuang glycoside or cornflower-3-Sang Bu bisglycoside, and also significantly stronger than that of the positive control drug dipotassium glycyrrhizinate; this illustrates: the synergistic soothing effect can be achieved by combining cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bu disaccharide glycoside; the composition obtained by combining cyanidin-3-Sang Bushuang glycoside and delphinidin-3-Sang Bu disaccharide glycoside has excellent relieving effect.
EXAMPLE 6 anti-inflammatory Activity assay
Selecting 72hpf zebra fish with good development, putting 15 zebra fish into each hole, and repeating three zebra fish holes in each group. A control group, an experimental group, a model group and a positive drug group are arranged. The wells were blotted with 1ml buffer, control and model groups were added, 1ml of different concentrations of the test sample drug was added, and 1ml of the corresponding positive control was added to the positive control group. Placing into an incubator for culturing for 2 hours. After 2h, the plates were removed and each well was washed twice with holt-buffer, 1ml of holt-buffer solution was added to the blank, and 1ml of 20. Mu.M copper sulfate solution was added to each well of the model and drug-treated positive controls. And (5) placing the mixture into an incubator for culturing for 2 hours, and taking photos. The results in FIG. 2 show that the composition described in example 4 (labeled anthocyanin in the figures) has a strong good anti-inflammatory effect and shows good activity at 31ug/ml, and the positive control is 10. Mu.M dexamethasone.
EXAMPLE 7 antioxidant Activity assay
Selecting screened fish eggs with the height of 24hpf, 15 fish eggs per hole in a 24-hole plate, 3 fish eggs per hole in each group, and setting a blank group, a model group, a positive control group and an experimental group. After removing the residual buffer water in the wells, 1ml of holt-buffer solution was added to the blank, 1ml of 2mM t-butyl hydroperoxide solution was added to the model, 1ml of 2mM t-butyl hydroperoxide glutathione solution was added to the positive control, and 1ml of 2mM t-butyl hydroperoxide test sample solutions of different concentrations were added to the test. The interval between the second hole and the previous hole is about 20-25min during dosing. Culturing in incubator for 2d. The results in FIG. 3 show that the composition described in example 4 (labeled anthocyanin in the figures) has greater antioxidant activity than the positive glutathione (7 ug/ml) at a concentration of 125 ug/ml.
Claims (6)
1. Use of a composition for the preparation of a product having a soothing effect; the composition comprises the formula
Compounds of the structures shown in I and II;
A formula I;
Formula II.
2. The use according to claim 1, wherein the weight ratio of the compounds of the structures of formula i and formula II is 1-5:1-5.
3. The use according to claim 2, wherein the weight ratio of the compounds of the structures of formula i and formula II is 1-3:1-3.
4. The use according to claim 2, wherein the weight ratio of the compounds of the structures of formula i and formula II is 2-3:1.
5. Use of a composition comprising a compound having the structure of formula i and formula II for the preparation of a product having both soothing, anti-inflammatory and anti-oxidant effects;
A formula I;
Formula II.
6. The use according to any one of claims 1 to 5, wherein the product is a cosmetic, skin care product or pharmaceutical product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211340546.2A CN115636857B (en) | 2022-10-28 | 2022-10-28 | Compound, composition, extract and application thereof in preparation of products with relieving effect |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211340546.2A CN115636857B (en) | 2022-10-28 | 2022-10-28 | Compound, composition, extract and application thereof in preparation of products with relieving effect |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115636857A CN115636857A (en) | 2023-01-24 |
| CN115636857B true CN115636857B (en) | 2024-09-10 |
Family
ID=84946354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211340546.2A Active CN115636857B (en) | 2022-10-28 | 2022-10-28 | Compound, composition, extract and application thereof in preparation of products with relieving effect |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115636857B (en) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4320009A (en) * | 1977-07-25 | 1982-03-16 | Frito-Lay, Inc. | Processed anthocyanin pigment extracts |
| US7820207B2 (en) * | 2007-03-15 | 2010-10-26 | Omnica Gmbh | Stabilized anthocyanin compositions |
| FR3031458B1 (en) * | 2015-01-12 | 2019-06-07 | Biolie | SALAD EXTRACTS, COMPOSITIONS AND USES |
| CN109200045A (en) * | 2017-06-30 | 2019-01-15 | 中国科学院西北高原生物研究所 | Application and pharmaceutical composition of the Anthocyanin-rich Extract in the pharmaceutical composition of preparation prevention and treatment anthracene nucleus medicament myocardiocyte toxicity |
| CN107522761B (en) * | 2017-08-24 | 2019-06-14 | 浙江大学 | A kind of method and its hypoglycemic purposes isolating and purifying delphinidin -3-O mulberry cloth disaccharide glycosides |
| EP3784251A1 (en) * | 2018-04-23 | 2021-03-03 | Evonik Operations GmbH | Preparations containing anthocyanins for use in the prevention and treatment of cardiovascular diseases |
| CN108558971A (en) * | 2018-05-31 | 2018-09-21 | 福州大学 | A kind of preparation method of roselle anthocyanin |
| CN109134560B (en) * | 2018-10-29 | 2020-08-14 | 湖南华诚生物资源股份有限公司 | Method for extracting anthocyanin from roselle calyx |
-
2022
- 2022-10-28 CN CN202211340546.2A patent/CN115636857B/en active Active
Non-Patent Citations (3)
| Title |
|---|
| 李成惠.玫瑰茄花青素提取及分离系统技术研究.《中国优秀硕士学位论文全文数据库 工程科技I辑》.2018,第B024-386页. * |
| 玫瑰茄花青素提取及分离系统技术研究;李成惠;《中国优秀硕士学位论文全文数据库 工程科技I辑》;20180415;第B024-386页 * |
| 玫瑰茄黄酮超声波辅助提取及其抗氧化活性;王丽岩 等;《吉林农业大学学报》;20161231;第38卷;第117-121页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115636857A (en) | 2023-01-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5324084B2 (en) | Cowberry extract and its production method and use | |
| JP2009013159A6 (en) | Cowberry extract and its production method and use | |
| US20100041877A1 (en) | Method for producing purified anthocyanin | |
| US6264853B1 (en) | Complex containing lignan, phenolic and aliphatic substances from flax and process for preparing | |
| JP2004521934A (en) | Methods for obtaining lignans, pharmaceutical compositions and uses thereof | |
| US20130131328A1 (en) | Process for producing refined nutraceutic extracts from artichoke waste and from other plants of the cynara genus | |
| CN111217864B (en) | Extraction method of green pepper alkaloid | |
| WO2022215441A1 (en) | Novel polyphenol compound | |
| CN105998103A (en) | Chestnut flower activated extract and preparation method and application thereof | |
| KR101737556B1 (en) | Composition for ameliorating oxidative stress comprising extacts from processed Polygoni Multiflori Radix | |
| CN115636857B (en) | Compound, composition, extract and application thereof in preparation of products with relieving effect | |
| CN111825647B (en) | Method for extracting anthocyanin from aronia melanocarpa | |
| KR100817876B1 (en) | Isolation process for proanthocyanidin from the bark of pine tree | |
| CN108997359B (en) | Method for extracting chlorophyll from stevioside production waste residues | |
| WO2022254868A1 (en) | Novel isoflavone compound | |
| EP4349844A1 (en) | Novel phenylpropanoid compound | |
| CN101810317B (en) | Preparation method of canophyllic polyphenol and application thereof | |
| KR101437814B1 (en) | Food Composition Comprising Fucoxanthin Derived from Microalgae and The Preparation Method thereof | |
| CN110680847A (en) | Method for extracting and purifying cannabinoids | |
| CN111228356B (en) | Method for purifying green pepper alkaloid | |
| KR102521125B1 (en) | Food Composition Comprising Fucoxanthin | |
| KR20200016101A (en) | Method for producing the extracts of natural material using ethyl lactate | |
| KR20050097698A (en) | A method for producing oleanolic acid and ursolic acid from persimmon peel | |
| CN111184793B (en) | Green pepper extract and application thereof | |
| JP7015775B2 (en) | Polyphenol derivative exhibiting gene repair action |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| TA01 | Transfer of patent application right | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20230809 Address after: No. 221, 2nd Floor, No. 35 Huajing Road, Huajing New City, No. 105 Zhongshan Avenue, Tianhe District, Guangzhou City, Guangdong Province, 510665 Applicant after: Haisi Chuangyan Pharmaceutical Technology (Guangzhou) Co.,Ltd. Address before: 518128 302 Huijige, Sanwei Community, Hangcheng Street, Bao'an District, Shenzhen City, Guangdong Province Applicant before: Shenzhen qishengwei Biotechnology Co.,Ltd. |
|
| GR01 | Patent grant | ||
| GR01 | Patent grant |